ISOACTEOSIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C29H36O15
Molecular Weight	624.5871
Optical Activity	UNSPECIFIED
Defined Stereocenters	10 / 10
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](COC(=O)\C=C\C3=CC=C(O)C(O)=C3)O[C@@H](OCCC4=CC=C(O)C(O)=C4)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O

InChI

InChIKey=FNMHEHXNBNCPCI-QEOJJFGVSA-N

InChI=1S/C29H36O15/c1-13-22(35)24(37)25(38)29(42-13)44-27-23(36)20(12-41-21(34)7-4-14-2-5-16(30)18(32)10-14)43-28(26(27)39)40-9-8-15-3-6-17(31)19(33)11-15/h2-7,10-11,13,20,22-33,35-39H,8-9,12H2,1H3/b7-4+/t13-,20+,22-,23+,24+,25+,26+,27-,28+,29-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C29H36O15
Molecular Weight	624.5871
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	10 / 10
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28441758 | https://www.ncbi.nlm.nih.gov/pubmed/28616865

Isoacteoside (2-(3′,4′-dihydroxyphenyl)ethyl 6-O-caffeoyl-3-O-(α-l-rhamnopyranosyl)-β-d-glucopyranoside), a phenylethanoid glycoside isomeric to acteoside, exists in various plants, such as Cistanches spp., Castilleja spp. and Plantago spp. It exerts wide range of pharmacological activity including anti-inflammatory and cytoprotective actions.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Potency
Toll-like receptor 4 6 Target ID: CHEMBL5255 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28616865	Inhibitor 8504
Aldose reductase 45 Target ID: CHEMBL2622 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24288293	Inhibitor 8504	0.83 µM [IC50]
Xanthine dehydrogenase 33 Target ID: CHEMBL1929 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10630118	Inhibitor 8504	45.48 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Inflammatory diseases 15 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28616865 https://www.ncbi.nlm.nih.gov/pubmed/25975581	Primary		Preclinical	Unknown Approved Use Unknown
Alzheimer’s disease 278 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28441758	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Isoacteoside, a dihydroxyphenylethyl glycoside, exhibits anti-inflammatory effects through blocking toll-like receptor 4 dimerization.	2017-09	28616865
Acteoside and Acyl-Migrated Acteoside, Compounds in Chinese Kudingcha Tea, Inhibit α-Amylase In Vitro.	2017-06	28486011
Acteoside and Isoacteoside Protect Amyloid β Peptide Induced Cytotoxicity, Cognitive Deficit and Neurochemical Disturbances In Vitro and In Vivo.	2017-04-24	28441758
Inhibitory activities of acteoside, isoacteoside, and its structural constituents against protein glycation in vitro.	2013-12	28510849
HIV-1 integrase inhibitory phenylpropanoid glycosides from Clerodendron trichotomum.	2001-08	11534758

Patents

Sample Use Guides

In Vivo Use Guide

Rats: 2.5 or 5.0 mg/kg

Route of Administration: Oral

In Vitro Use Guide

Isoacteoside inhibited D-GalN-induced death of hepatocytes (IC50-5.3 microM) and reduced TNF-alpha-induced cytotoxicity in L929 cells (IC50-22.7 microM).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 20:12:14 GMT 2025` Edited by `admin` on `Mon Mar 31 20:12:14 GMT 2025`
Record UNII	588LJK42AP
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ISOVERBASCOSIDE

Preferred Name

English

ISOACTEOSIDE

Common Name

English

NSC-729649

Code

English

.BETA.-D-GLUCOPYRANOSIDE, 2-(3,4-DIHYDROXYPHENYL)ETHYL 3-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-, 6-((2E)-3-(3,4-DIHYDROXYPHENYL)-2-PROPENOATE)

Systematic Name

English

Code System Code Type Description

CAS

61303-13-7